The Shortest (Four‐Step) Total Synthesis of the Eight‐Membered Cyclic Ether (rac)‐ and (–)‐cis‐Lauthisan. Issue 28 (22nd August 2013)

• Record Type: Journal Article
• Authors: Hernández‐Torres, Gloria; Mateo, Julio; Urbano, Antonio; Carreño, M. Carmen
• Is Part Of: European journal of organic chemistry. Issue 28(2013)
• Page Start: 6259
• Page End: 6262
• Publication Date: 2013-08-22
• Subjects: Natural products -- Total synthesis -- Cyclization -- Stereoselectivity -- Cyclic ethers; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201301042
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: Access to the eight‐membered cyclic ether ( rac )‐ and (–)‐ cis ‐lauthisan was achieved in two complementary ways in only four steps for the longest linear sequence by starting from commercially available materials. The sequence features a cis ‐stereoselective reductive cyclization as the key step. Abstract : Acetylide opening of two epoxides followed by the Rh‐catalyzed 1, 4‐addition of the resulting homopropargylic carbinols to the corresponding enones allows the rapid construction of the carbon skeleton of ( rac )‐ and (–)‐ cis ‐lauthisan, which are synthesized after triple‐bond reduction and cis ‐stereoselective reductive cyclization of the two regioisomeric hydroxy ketones formed.